Making the most of your one-on-one with your manager or other leadership

As many offices go fully remote, learning how to approach key meetings with your manager can pay big dividends.

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Taking advantage of one-on-one time with your leaders is essential to your career success. In a time when so many of us are remote, and there are fewer opportunities for serendipitous chats in the hallway or conversations over lunch, this is more true than ever.

I have had one-on-one meetings with my direct reports and skip levels since I moved into leadership, and honestly, they are often the favorite parts of my day. I tell my team members that this is their time to get my undivided attention, and they should take advantage of it. I try very hard not to use it for something I need to talk about. When there is a topic I need to introduce, I warn them at the beginning and reserve time at the end for it. The best conversations are the ones where someone comes prepared with an agenda, sometimes they even send it to me in advance.

So, how can you ensure both you and your manager get the most of a one-on-one? First, make sure you have them on a recurring and ideally regularly scheduled basis. You need to develop trust and be able to measure progress so that the conversations feel connected.

If you don’t have this kind of check-in right now, ask for it. If they keep getting canceled, reach out and ask how you can ensure they happen. Consider looking to get time with other members of the leadership team on a semi-regular basis. Since everyone at Stack Overflow, including the senior leadership team, is now 100% remote, I make sure to dedicate time on my calendar to office hours for employees to discuss anything. For a more casual environment, once a month senior leadership member hosts our company-wide bev bash.

Ok, you’ve put in the work and your manager has made time for you on their calendar. How do you make the best use of it? Be prepared.

Try not to use this time to give basic status updates; send those by email or other methods. Instead, think about the areas you need their support, advice, or a decision. Also, think about where you want them to have information or knowledge about you. The big topics you should think about in preparing your agenda are:

  • Current projects — Do you need their support in helping to remove an obstacle? Do you need them to make a decision where there isn’t an obvious solution to move forward? Does the team need more members or additional skillsets to succeed?
  • Feedback — Ask for feedback every opportunity that you get with leadership. If they don’t have anything to share, keep asking and they will be better prepared in the future. What have you done really well in the last couple of weeks? Are there situations where they think you could have done better? If so, get details? What do they think is the biggest strength you bring to the role? What area do they think you should focus on improving to help you succeed or progress in your role? What do they think could be holding you back?
  • Professional development — Have you received feedback that you aren’t sure how to best act on? Are you unsure of how to progress in your current path or if you want to move to another path/role? Do you have skills that you want to improve but are not sure how to approach it? Are there conferences, classes, or workshops that you want to participate in coming up?
  • Future opportunities — Have you identified specific types of projects that you want to get exposure to in order to broaden or deepen your knowledge? Is your manager aware of this desire? Do you want to get experience in a leadership position in a future project? Are you interested in other teams or roles that they should know about?

Go through this list each time as you prepare your agenda. Everyone is busy and has a lot on their mind. To make the most efficient use of this time, be specific and succinct. What decision do they need to make and what information do they need to make it? What knowledge do you want them to remember about you so they can support your career progression? What specific action do you want them to take to support the success of your team? Of course, thank them for their time, support, and advice at the end of each meeting. We all have a million ways to spend our time, and they choose to invest some of their time in you.

A version of this post first appeared on Teresa's personal blog.

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